1. Field of the Invention
This invention relates to novel substituted phenyl carbamates and thionocarbamates [hereinafter collectively called "substituted phenyl (thiono)carbamates"] represented by the general formula (I) ##STR1## wherein X is an oxygen or sulfur atom or a vinylene group, l and m each is an integer of 1 to 4, n is an integer of 0 or 1, the heterocycle comprising the nitrogen atom, the two alkylene chains and X is 5- to 7-membered, the two alkylene chains each may be branched, Y.sup.1 is a halogen atom, Y.sup.2 is a hydrogen or halogen atom, R is an alkyl group, which may be interrupted by one or more oxygen atoms, or an optionally halo-substituted alkenyl or alkynyl group and Z is an oxygen or sulfur atom; herbicidal compositions containing the same as active ingredients and a method of controlling weeds using said substituted phenyl (thiono)carbamates.
2. Description of the Prior Art
It is known that certain substituted phenyl carbamates, such as 4-chlorophenyl 1-pyrrolidinecarboxylate and 2,4-dichlorophenyl 1-pyrrolidinecarboxylate, can inhibit the growth of weeds on the cultivated field in pre-emergence application and can selectively control Echinochloa species (barnyard grass, etc.) at their growth stage in the paddy filed (cf. U.S. Pat. No. 3,142,556 and Japanese Patent Application Publication No. 17,157/1971). However, these substituted phenyl carbamates are not so satisfactory in their herbicidal activity. Certain substituted phenyl thionocarbamates, such as 0-(4-chlorophenyl) 1-pyrrolidinecarbothioate and 0-(3-methoxyphenyl) 1-pyrrolidine-carbothioate, are also known to be herbicidally active against weeds on the cultivated field (cf. U.S. Pat. No. 3,217,002). However, these substituted phenyl thionocarbamates are impracticable because of their insufficient herbicidal activity and strong phytotoxicity to the desired crop plants.